History of Benzene

1
History of Benzene
1824 - 1825 Isolated from burnt whale oil by
Michael Faraday 1834 Eilhardt Mitscherlich finds
benzene has formula of C6H6 1861 Loschmidt
proposes structure for benzoic acid and aniline
2
History of Benzene
1824 - 1825 Isolated from burnt whale oil by
Michael Faraday 1834 Eilhardt Mitscherlich finds
benzene has formula of C6H6 1861 Loschmidt
proposes structure for benzoic acid and aniline
3
History of Benzene
1865 Kekule has a dream 1865 Kekule invokes
sausage diagrams Bulletin de la Société Chimique
de France, 3, 98 (1865)
4
History of Benzene
1865 Kekule has a dream 1865 Kekule invokes
sausage diagrams Bulletin de la Société Chimique
de France, 3, 98 (1865)
1866 Kekule introduces ring model for benzene
5
Alternate Benzene Structures
6

Fig. 15-2, p. 521
7

Hückels Rules for aromaticity
8

Benzene electron distribution map
p. 521
9

Fig. 15-12, p. 532
10

Hückels Rules for aromaticity
Aromaticity vs. antiaromaticity
11

p. 523
12

p. 524
13

Hückels Rules for aromaticity
Aromaticity vs. antiaromaticity
Why 4n 2 for aromatic and 4n for
antiaromatic? Frosts cycle
14

Benzene Molecular Orbitals
Fig. 15-3, p. 522
15
Cyclopentadienyl ions
16

Fig. 15-11, p. 531
17

Fig. 15-5, p. 526
18

Fig. 15-7, p. 527
19

Fig. 15-9a, p. 529
20

Fig. 15-9b, p. 529
21
5. 14-annulene

1. Aromatic
2. Antiaromatic
3. Neither

22
Pyridyl DHA Targets
23

Fig. 15-14, p. 535
24

p. 535
25

p. 540
26

p. 535
27
Aromatic Biomolecules

1. Amino acids
2. Nucleic acids

28

Fig. 15-8, p. 528
29

Fig. 15-9, p. 529
30

p. 533
31

p. 529
32

p. 533
33

p. 530
34

p. 540
35

p. 541
36
p. 337
37
p. 338
38
Table 9-2, p. 337
39
Summary
40
Fig. 9-16, p. 338
41
p. 340
42
p. 345